He’s angry that I dated other people

I am in my mid 20s and a young professional. "Jack" is 25. We both live in Boston. Last fall, after five years together, Jack dumped me. It wasn't completely out of the blue. We had been unhappy for a while but it didn't hurt any less. When he broke up with me, he was very final, he said his goodbyes, ignored my pleas to work out our differences, and stopped answering my calls and texts. During the early break-up stages, I had a major family emergency. Naturally I reached out to him for support, but he was not there to help. I had no choice but to pick up the pieces of my life and enjoy being in my early 20s in the city.

Fast forward to the spring. After almost six months of not speaking, Jack worked his way back into my life. I had never stopped loving or caring for him and although I was hurt by his inability to try to push through our faults, I realized that the time apart had been the best thing for us. I couldn't have been happier that he wanted to give it another go.

The inevitable catch is that Jack is very conservative, and when we were getting back together he made a very bold statement that if I had "dated" or "been with" anyone while we were apart, he wouldn't be able to be with me. I attempted the response of "we weren't together so I'm not talking about it," but he refused to accept that as an answer. So I did what I thought was right and went with the "what he doesn't know won't hurt him" strategy. Although he really pushed the issue and begged for my honesty, I flat out lied to his face when he asked me if there had been anyone else. I wanted him back so badly that I truly didn't feel like I had a choice.

Last Saturday night, after four months of bliss and far too many cocktails, he brought up that he had heard I was lying about what had happened during our time apart. I reluctantly confessed that I had lied and that there had been other people.

To say he flipped out would be an understatement. I was called every name in the book, my belongings were dropped off at my house, and I have been getting seething and hurtful texts ever since. I don't know if he is more mad about the lying (an admitted mistake on my part) or about what I did. I think both. But he has called it quits AGAIN. I told him that adults don't just walk away from relationships, they work through problems, but he has stated that he doesn't think that he can ever trust me again and would never want to be intimate now that he knows I have been with other people.

I want to be with him more than anything, but after his recent proclamations about not being able to forgive me, I am not sure where to go from this point. Do I continue my apologies and pleas or do I walk away for a final time?

– Reluctantly in love, Boston

If you have to lie to maintain a relationship, it's probably not a relationship worth having, RIL. Had you written to Love Letters four months ago, I would have told you not to get back together with this guy.

He had no right to expect you to stay out of the dating game after he bailed on you. You say that he's "conservative," but he sounds selfish and irrational.
If he was worried about his health, he could have asked you to take an STD test. His real concern has been his own weird definition of purity and your commitment to him when he wasn't committed to you.

You say that you want to be with him more than anything, but he hasn't earned that loyalty. He ditched you, made irrational demands, and then ditched you again. This relationship isn't worth saving.

My advice? Let this go. Allow yourself to get angry. Yes, you messed up by lying (please, never do that again), but he made mistakes too. Unless this guy acknowledges that he also owes you a serious apology, it's over.

Readers? Who's at fault here? Does he have the right to be angry? Does she? Is there something worth saving? Help.